EP 1003717 A1 20000531 - PREPARATION AND USES OF HYDROCARBYLNITRONES
Title (en)
PREPARATION AND USES OF HYDROCARBYLNITRONES
Title (de)
VERFAHREN UND VERWENDUNG VON HYDROCARBYLNITRONEN
Title (fr)
PREPARATION ET UTILISATIONS D'HYDROCARBYLNITRONES
Publication
Application
Priority
- US 9816110 W 19980804
- US 90552597 A 19970804
Abstract (en)
[origin: WO9906362A1] Nitrones are produced by reaction of primary amine with aldehyde or ketone, in the presence of a transition metal-containing oxidation catalyst, and a peroxidic compound. The nitrone can then be reacted with a vinylaromatic compound to produce a 2-hydrocarbyl-5-arylisoxazolidine. Both such reactions can be conducted concurrently by including the vinylaromatic compound in the initial reaction mixture. Hydrogenation of the 2-hydrocarbyl-5-arylisoxazolidine, e.g., using hydrogen and a palladium-carbon catalyst, forms an N-hydrocarbyl-3-aryl-3-hydroxypropylamine. Such reactions enable, inter alia, synthesis of the racemic hydrochloride salt of N-methyl-3-phenyl-3-[4-trifluoromethyl]-propylamine, known generically as fluoxetine hydrochloride, a widely used antidepressant.
IPC 1-7
IPC 8 full level
C07C 217/26 (2006.01); C07C 291/02 (2006.01)
CPC (source: EP US)
C07C 217/26 (2013.01 - EP US); C07C 291/02 (2013.01 - EP US)
Designated contracting state (EPC)
BE CH DE ES FR GB IT LI NL
DOCDB simple family (publication)
WO 9906362 A1 19990211; EP 1003717 A1 20000531; US 5998627 A 19991207
DOCDB simple family (application)
US 9816110 W 19980804; EP 98938289 A 19980804; US 90552597 A 19970804